


ONE SHOT - Hailey and Jay - Caught

by ChiHard



Series: One Chicago - ONE SHOTS [3]
Category: Chicago PD (TV)
Genre: F/M, upstead on a date
Language: English
Status: Completed
Published: 2020-07-20
Updated: 2020-07-20
Packaged: 2021-03-04 17:34:46
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,429
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25400221
Author URL: https://archiveofourown.org/users/ChiHard/pseuds/ChiHard
Summary: voight driving past while upstead are on a secret date
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton, Upstead - Relationship
Series: One Chicago - ONE SHOTS [3]
Series URL: https://archiveofourown.org/series/1789906
Comments: 2
Kudos: 48





	ONE SHOT - Hailey and Jay - Caught

**Author's Note:**

> prompt from @/dav38125 on twitter thank you <3 
> 
> send me prompts on twitter @haileysburgess

They had decided on a small restaurant for their date tonight, they made sure to choose a restaurant that was as far away from Molly's as possible as that's where everyone they knew would be on a Saturday night. They were currently secretly dating, not a soul knew and they wanted to keep it that way for now. That's why just to be safe they decided to travel just outside of the city for their date. Yes it was quite out of their way but it was worth it to have a low-key carefree date together without the fear of people they know seeing them. They had only been dating for 2 months but it felt like a lot longer. They had both been dancing around their feelings for so long. Hailey was actually the one who had found the restaurant when looking for a place to take jay out to, she thought that it was low-key and comfortable enough that they would both be able to relax and enjoy the rare weekend off.

They had decided that Jay would pick Hailey up at 7pm so that they should be able to make it to the restaurant by 7:30pm and because Hailey knew Vanessa was going to be out of the house by 6pm so she would have plenty of time to get ready. Jay had decided to wear a pair of black jeans with a light grey polo shirt that made the outfit look slightly smarter but he also knew that Hailey loved that shirt on him. He checked himself in the mirror one last time before leaving his apartment and driving over to Hailey's. 

Hailey had planned on surprising Jay with her outfit choice tonight, she wasn't a 'typical' women she didn't own lots of dresses, makeup, jewellery or high heels and the limited ones she did were for undercover purposes only and she would never voluntarily wear. But when she was walking down the street after coming out of the gym a certain green wrap dress with a small pastel yellow flower pattern had caught her eye in the shop window. She had no idea why she wasn't even a big fan of dresses but for some reason she was drawn to this one. It ended with her walking out of the shop 20 minutes later with a small bag in hand and $32.19 poorer.

As she looked in the mirror the dress fitted her really well but it was still loose enough that she felt comfortable. It came to just above her knee and had a deep neckline that wasn't too revealing but it gave enough to the imagination and she was sure Jay would like it. She decided on a simple pair of silver stud earrings and a silver necklace with a little heart charm that Jay had brought her for her birthday last month. Her hair had been neatened a little from her usual frizzy curls look and sat a few inches below her shoulders. She was just putting on one last stroke of mascara when she heard a knock at her door, she grabbed her flats and made her way downstairs.

When she opened the door she was met by the sight of her handsome boyfriend looking great in a casual pair of jeans and her favourite polo shirt of his. He seemed slightly shocked and speechless at her outfit choice so she tried to break the air.

"So are we going to go to dinner or are you just gonna stand here looking at me" she joked at him.

"No...um...wow you- you look beautiful it's just this is something so new for you and you look truly amazing. Wow Hailey" he stuttered out once he gained control of his thoughts.

"I know it is but I kinda like it but you better not get used to this" she laughed.

She shut her door and locked it before walking with Jay to his truck. The drive went quite quick as they filled the journey with conversation and laughter. When they arrived at the restaurant Jay found a parking space slightly down the street and they began walking towards. The restaurant looked old and worn yet bright and warm and comfortable. They were seated right in front of the large glass window on a small two person table. The table had a mason jar in the middle with a single rose in it with small tea light candles around the jar to add a romantic feel to the atmosphere. 

Once they were both seated they had a quick look through their menus and ordered. Jay decided to order mushroom risotto and Hailey decided on the chicken penne carbonara and they both ordered red wine to go with it.

As they sat waiting for their dishes Jay was holding Hailey's left hand that laid on the table slowly drawing lines over it with his thumb. They talked about some casual topics happily laughing at parts of their conversation. Before they knew it the dishes were placed in front of them as well as a refill on their wine.

They were almost finished with their dishes when Jay suddenly stopped eating and just looked at Hailey, which caused her to stop eating too and look at Jay.

"Hey you alright why'd you stop?" she asked with concern laced in her voice.

Jay grabbed her hand again repeating the same rubbing motion with his thumb and locked his eyes on hers.

"I love you so much Hailey" he softly spoke.

"I love you too Jay" she replied.

Jay leaned in and moved his hand up to the back of her head and brought her closer before capturing her lips in a deep kiss. They were suddenly both lost in their own little world that they didn't notice anything or anyone around them especially the eyes looking in from the car in the middle of the street.

___________________________________________

Hank Voight had decided to visit an old friend who lived on the outskirts of Chicago as he had given the unit and himself the weekend off as they normally didn't. He had overhead the unit talking in the bullpen about hitting Molly's early on Saturday and meeting up with a few people from 51 and med and he was happy they all had plans and got along so well with the others.

He had heard Jay say that he was unable to join as he was visiting his brother who also had the weekend off and they were going to hang out and watch some ice hockey because they both didn't feel like hitting up the bar. Hailey had said she also had plans this weekend of travelling to meet up with some old college friends who were in town.

Hank decided to drive up early to visit Darrell as he wanted to spend the most part of the day with is old friend. He decided to start heading back to the city just before 8pm thinking he would miss the weekend traffic. Unfortunately he was wrong and ended up stuck in his car not moving through a busy town street, both sides filled with bars and restaurants explaining the traffic.

As he sat outside one restaurant he looked in at the large glass window and was completely shocked by what he saw. At first he thought it was just a play on his eyesight until he blinked a few times and rubbed his eyes but he was definitely not seeing things.

In the front window sat Hailey Upton and Jay Halstead. He thought for a second maybe both their plans were cancelled and they decided to meet for dinner but why would they meet so far away from the city? This was obviously a date especially by the way Hailey was dressed he never thought he would see the day she wore a dress not for undercover and the fact that they were holding hands.

He watched as they held hands and then he saw them lean in and begin to kiss. He quickly looked away not believing what he had just witnessed and not wanting to see two of his unit members doing what was clearly supposed to be unknown to others. Luckily the traffic started moving and he could move away and start making his way back home.

As he drove home his mind still couldn't believe what he had just seen. Now he had to wait until Monday to talk to them, and he was not looking forward to it.


End file.
